Tetrahedron

Tandem aza-Michael additions under high pressure: a shortcut to the azanorbornyl skeleton

AY Rulev, N Yenil, A Pesquet, H Oulyadi, J Maddaluno

Index: Rulev, Alexandre Yu.; Yenil, Nilgun; Pesquet, Anthony; Oulyadi, Hassan; Maddaluno, Jacques Tetrahedron, 2006 , vol. 62, # 23 p. 5411 - 5416

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Citation Number: 18

Abstract

The hyperbaric aza-Michael addition of mono-and diamines on α, β-unsaturated β, β- disubstituted mono-and diesters has been studied. While in the case of monoester, this reaction provides a β-aminoester presenting a quaternary center, a direct and efficient access to diester or lactams featuring an azanorbornyl skeleton was obtained when starting from a diester, following an unprecedented double aza-Michael addition.